Day 1

Although there are many positive things to say about this beautiful land, it must be said that it is not well connected, so wherever you’re coming from, it will take you a long time to get here. After long hours of travel you probably won’t feel like driving another hour to reach your dinner, so I recommend choosing something nearby your accommodation. If you’re staying in Montalcino (some great properties on airbnb, both in the town and outside, which have the bonus of having gardens) I suggest starting your evening with a walk above the town’s ancient walls, as you admire the sun setting over the distant hills. Then, make your way up the main street, Via Matteotti, until you reach the main square, with the Palazzo dei Priori sitting right in the middle. To the left, a picturesque loggia – the perfect place to enjoy a glass of Rosso di Montalcino or Brunello di Montalcino (if you’re ready to dive into the local wine culture). Sit inside if you want to admire the beautiful landscape or outside if you feel like doing some people watching. Once you’re done, make your way up the town, towards the Fortezza and enjoy a plate of Tuscan salumi and a dish of pinci con le briciole at Porta al Cassero, a traditional osteria with a great atmosphere.

Day 2

After a relaxing breakfast, jump in your car and make your way to San Quirico, an idyllic town with a history dating back to the Middle Ages, when textile merchants on their way to and from Rome would stop and rest. On the carriage way that leads to San Quirico, stop where you see two parking spaces on either side of the road. A 20 minute walk from the road is a beautiful cluster of trees known as the Cipressini – one of the most photographed places in the whole of Val d’Orcia! Although it is a “touristy” destination, the short walk is a lovely way to start your day, and you can admire the iconic Tuscan cypresses. Once you’ve taken all the pictures to make your friends on instagram jealous, proceed to San Quirico and stroll through the main pedestrian street, Via Dante Alighieri. If the Horti Leonini are open, be sure to pay them a visit. A beautiful Italian-style private garden well-known for being one of the first public gardens (and not connected to a mansion). Then drive around the various hamlets dotted above the hills, like Monticchiello, and walk through the town as you admire the immaculate houses and tiny winding streets. Stop for lunch at the panoramic Osteria La Porta which has a modern interpretation of local and traditional Tuscan products. From Monticchiello drive down through a strada bianca (a country road off the beaten path) to Pienza where you can enjoy a delicious ice cream at Buon Gusto Gelateria or an aperitivo at Idyllium, above the city’s ancient walls overlooking the whole of Val d’Orcia and Monte Amiata in the distance. If you feel like doing some more sightseeing, Palazzo Piccolomini and its beautiful gardens are worth a visit. For dinner head down the hill to Bagno Vignoni, for an outdoor (in summer) and relaxing dinner at the Osteria del Leone.

Day 3

For your last half-day in Val d’Orcia, you simply need to visit a winery to taste some Brunello and Rosso di Montalcino. Working in a winery myself, I’m (obviously) going to recommend Podere Le Ripi. A medium sized, biodynamic winery immersed in the mediterranean macchia. Sustainable, interesting and delicious wines paired with unique and innovative architecture make it the perfect place to visit. As you make your way to lunch, stop for a quick visit at the Abbazia di St. Antimo, a medieval abbey which used to be in control of the whole of Val d’Orcia, filled to the brim with history. As your last gastronomic stop for the weekend, drive to the town of Sant Angelo in Colle (a 10 min drive from Montalcino) for lunch at Trattoria Il Pozzo, a traditional restaurant with a great selection of dishes and wine. 

There are so many more places to see, more foods to try that I would love to tell you about but it would be simply too much for a 3 day stay! Who knows, I might make another one soon… 

Where to eat 

Porta al Cassero – rustic osteria in Montalcino’s pedestrian centre, serving local cured meats and cheeses and traditional pasta dishes. 

Alle Logge di Piazza – great selection of local and international wines in Montalcino’s main square, overlooking Val d’Orcia on the opposite side. 

Osteria La Porta – quaint osteria serving reinterpreted traditional dishes with a breathtaking view of Val d’Orcia, situated in the tiny hamlet of Monticchiello. 

Buon Gusto Gelateria – delicious, artisanal gelato in Pienza’s centre. 

Idyllium – delicious drinks and bites overlooking Val d’Orcia and Monte Amiata in Pienza, just below the ancient walls of Palazzo Piccolomini. 

Osteria del Leone – possibly my favorite restaurant in Val d’Orcia serving local and reinterpreted dishes with an ever changing menu and great wine selection. 

Why Not Gelateria – excellent gelateria in Montalcino’s centre, open till late.